[HN Gopher] Tuesday was my last day as CEO of CircleUp
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       Tuesday was my last day as CEO of CircleUp
        
       Author : rmason
       Score  : 183 points
       Date   : 2020-10-15 20:05 UTC (2 hours ago)
        
 (HTM) web link (twitter.com)
 (TXT) w3m dump (twitter.com)
        
       | PragmaticPulp wrote:
       | The 6-page e-mail sent to the difficult former board member is
       | interesting:
       | https://docs.google.com/document/d/17tEc9ETL4tjfTmNbpwJJ5OSx...
       | 
       | Given that he posted the e-mail contents online and wrote it in a
       | way to narrate the board member's own bad actions, I'm assuming
       | the real intent to was to warn others against working with this
       | person. He stops short of naming the difficult board member, but
       | it wouldn't exactly be difficult to figure out who it was from
       | all the clues.
        
         | blantonl wrote:
         | Name the board member. The former CEO can be dignified by
         | keeping his name confidential , but this is a founder and
         | entrepreneur discussion forum and this deserves discussion
         | about this individual. It is also relevant to the story.
         | 
         | There is absolutely nothing wrong with knowing about, and
         | discussing who it is and possibly who else has had the same
         | experiences - as long as it isn't mudslinging but a
         | professional discussion. Similar to the letter.
        
         | sokoloff wrote:
         | I think just publishing the event without posting the email
         | leaves enough of a trail for another CEO to reach out and ask
         | "Hey, we're going to work with XYZ and know he used to be on
         | your board. Any advice for us?"
        
           | hinkley wrote:
           | Nobody likes to date people who are always trashing their
           | exes. Board members end up choosing the CEO, do they not?
           | There are degrees of dirty laundry airing that could end up
           | burning bridges with people you've never even met before.
           | 
           | Meanwhile the next CEO knows there's a rat, and can work out
           | for themselves who that might be before their first 100 days
           | are up, by which point most managers have been typecast.
           | After that it's very hard to fully take advantage of major
           | new insights you've had. It's an uphill battle to make major
           | changes to your style of management.
        
         | khaledtaha wrote:
         | Let's not do that. I'm incredibly appreciative of OPs
         | transparency here. As a person who is susceptible to the same
         | degree of stress and mental health toil, let's not make the
         | story about the investor but rather around the stresses of
         | being a CEO.
        
           | exolymph wrote:
           | You can't control what people are interested in, what they
           | want to know more about.
        
           | xyzzy_plugh wrote:
           | Why not both?
        
           | fairity wrote:
           | I agree that the problematic investor shouldn't be outed
           | here. The investor isn't here to defend himself, and outing
           | him will cause him irreparable (and perhaps undue)
           | reputational damage.
           | 
           | [edit] Is giving the accused a platform to defend himself
           | that unpopular of an opinion? Online shaming often gets out
           | of hand and goes too far. I recommend this TED talk: https://
           | www.ted.com/talks/jon_ronson_when_online_shaming_goe...
        
             | birdyrooster wrote:
             | What forum should he be outed in exactly?
        
               | fairity wrote:
               | There are a couple options that come to mind:
               | 
               | 1) Contact the accused party and ask him for a written
               | response. By giving him the opportunity to defend
               | himself, you get a more balanced view and decrease the
               | likelihood of cruel & unusual punishment.
               | 
               | 2) Out the investor in private forums where
               | data/information that arises after the publication of
               | this article can be fully considered. YC and many other
               | founder networks have investor databases for this
               | purpose.
        
               | munk-a wrote:
               | 1 isn't a terrible idea in most circumstances but with
               | investors you're more likely to get a C&D than a fair
               | response given the line of work and the importance of
               | reputation to the process.
               | 
               | 2 - no, I disagree strongly for two reasons:
               | 
               | Keeping information in a quiet private forum makes it
               | inaccessible to people at large. This means the next CEO
               | who runs up against this investor is mostly completely
               | unaware of their past actions.
               | 
               | And, honestly, hackernews is probably the single most
               | relevant forum you could find to discuss this on - it has
               | a general lean toward tech but it is run by ycombinator
               | which is specifically interested in all things
               | investment.
        
               | fairity wrote:
               | > Keeping information in a quiet private forum makes it
               | inaccessible to people at large. This means the next CEO
               | who runs up against this investor is mostly completely
               | unaware of their past actions.
               | 
               | I agree this is the downside of my proposed approach.
               | But, the alternative is a world where someone's
               | reputation can be irreparably damaged by unsubstantiated
               | claims made by one person.
               | 
               | Do you want to live in a world where someone's reputation
               | and livelihood can be destroyed by unsubstantiated
               | claims? You may think I'm overstating the potential
               | damage, but I think people generally underestimate the
               | damage the internet mob can inflict on a person.
        
               | munk-a wrote:
               | There are some societal tools that exist to fight against
               | baseless slander in a public forum but, tbh, the US has
               | resisted adopting those.
               | 
               | I would rather live in a world where the powerful can be
               | baselessly attacked compared to a world where the weak
               | are unable to fairly attack them - if we need to err on
               | one side or the other I prefer to put up with trolls and
               | scammers.
        
           | yowlingcat wrote:
           | Well. It seems like you can't narrate the latter without the
           | former. What would you propose?
        
         | anon_usr_134 wrote:
         | If you read the email it states that the investor was a lead.
         | Series A was led by USV and the email already ruled them out.
         | This investor sold right during or after the series C. might be
         | Brendan Dickinson from Canaan for the Series B.
        
         | maest wrote:
         | It's clear that people in the industry will be able to figure
         | out who the letter is addressed to - and I would be surprised
         | if the CircleUp CEO didn't realise this. So the censorship is
         | mostly for show.
         | 
         | The fact that the VC isn't named, makes it difficult for them
         | to reply in a public way and respond to some of those points.
        
           | PragmaticPulp wrote:
           | > and I would be surprised if the CircleUp CEO didn't realise
           | this.
           | 
           | That was the point I was trying to make:
           | 
           | The CEO went out of his way to make the board member as easy
           | to identify as he could, short of spelling his name out.
           | 
           | I'm not suggesting that people try to reverse engineer it,
           | but clearly the open letter was meant to be partially
           | retaliatory and partially a warning to others in this space.
        
             | sineus wrote:
             | Given the timeline, that he was lead investor, the name
             | length, the experience of the VC, the current and past
             | board members, it's easy to figure out the missing name.
             | https://en.m.wikipedia.org/wiki/CircleUp Confirms the name
             | which would also fit in the redacted parts of the email.
        
               | tschwimmer wrote:
               | Where are you seeing the current and past board members?
               | That's what I'm trying to diff against but I can't find
               | good sources.
        
               | ericjang wrote:
               | If you highlight the name, the highlighted text is
               | {{14}}. I don't think the lead investor's name is
               | necessarily 6 characters. FWIW, I was deeply curious
               | about who the investor was and spent some time
               | investigating who lead the fundraising rounds on
               | Crunchbase, but I couldn't narrow it down sufficiently.
        
               | [deleted]
        
           | skybrian wrote:
           | It seems like if many people don't know, then it actually
           | makes a difference that they don't know. I don't know the
           | details but it seems possibly important, not just for show?
           | 
           | See: https://en.m.wikipedia.org/wiki/Missing_stair
        
         | [deleted]
        
       | rmason wrote:
       | Here's the blog post that goes along with that tweet stream:
       | 
       | https://ryancaldbeck.medium.com/transitions-fa7ce4af435
        
         | a-posteriori wrote:
         | Adding the google cache. Looks like the medium is down.
         | 
         | http://webcache.googleusercontent.com/search?q=cache:-EgQnmp...
        
       | ghiculescu wrote:
       | I was wondering where I knew that name from... there's a module
       | about Ryan & CircleUp in the HBS Disruptive Innovation Course -
       | https://online.hbs.edu/courses/disruptive-strategy/
       | 
       | It was one of the more interesting companies profiled and I found
       | the module very cool. If you read this Ryan - thanks for being
       | part of it, and all the best for the future.
        
       | madrox wrote:
       | Reading this is like reading about my own experience. I went
       | through a similar period several years ago as an executive. I was
       | leading engineering for three separate products and dealing with
       | some very difficult stakeholders. I was also in a new
       | relationship that I was trying very hard to maintain. The stress
       | of all these things happening to me at once was colossal. I
       | experienced a constellation of bad health symptoms. What I can't
       | believe, in hindsight, was when I asked my doctor if this could
       | be stress related. He asked, "do you feel stressed?" I thought
       | for a second and said, "no."
       | 
       | I've never written anything about that time, despite wanting to,
       | but this is the thread I wish I could write. Details aside the
       | emotions are all the same. It felt cathartic to read this.
        
       | cthulhua wrote:
       | Wow, this really struck home with me. I left a FAANG about a year
       | ago to be employee #1 at a startup. 6 months ago, after some
       | headaches and vision issues, I was diagnosed with a brain tumor.
       | My work has been great through all this, but I can't imagine the
       | additional stress of being a CEO whilst dealing with all that.
        
       | duxup wrote:
       | I don't want to digress too much here but I thought this was
       | interesting:
       | 
       | > Believing that to attract a great CEO we would need more than
       | two years of runway
       | 
       | What is involved in this process that takes 2 years?
        
         | PragmaticPulp wrote:
         | > What is involved in this process that takes 2 years?
         | 
         | He's not saying the process will take 2 years.
         | 
         | He's saying that no reasonable CEO will sign on to a company
         | that is months away from going bankrupt. Two years of runway is
         | long enough for a new CEO to find their feet, set direction,
         | and work on profitability and/or fundraising.
         | 
         | If the CEO arrives with only a few months of runway, their
         | first tasks will be to cut burn rate by laying off many of the
         | employees. That doesn't create a good first impression.
        
         | bishnu wrote:
         | I think what he's saying is that no-one would be willing to
         | take over as CEO unless they had two years of runway ahead of
         | them.
        
         | skrtskrt wrote:
         | In addition to the other answers, it sounds like they knew they
         | needed more time to execute & validate the pivot.
         | 
         | Let the original founder/visionary execute the pivot and then
         | hand off the reins, rather than pull someone new in and try to
         | brain-dump how you want them to pull off the pivot that mostly
         | exists in your head.
        
         | codingdave wrote:
         | It isn't that the process takes two years - I'm guessing they
         | were talking more about being a good career move for a CEO
         | candidate:
         | 
         | A great CEO has many options in front of them of what to do
         | with their career. Asking them to take on a company that
         | doesn't have much runway limits the time they have to get in,
         | become the new leader, and mold the organization. Therefore, it
         | is not likely to be their best option, which means the
         | candidates who are interested are more likely to be not-so-
         | great CEO candidates.
        
           | duxup wrote:
           | Got it, that makes a lot more sense.
        
       | ProAm wrote:
       | Twitter is the worst for long form messaging.
        
         | Kiro wrote:
         | I agree that the UI sucks but I like the constraints. It gives
         | no room for filler text and every paragraph/tweet needs to have
         | its own point.
        
       | luminati wrote:
       | First thanks so much for writing this. The gilded world of
       | unicorn CEOs seems all roses and wine from the Techcrunch
       | armchair VC/outside world, so it was eye-opening to read an
       | intimate account of the cold, brutal reality of being one.
       | 
       | That said, I have one question. What on earth was the co-founder
       | doing? Isn't it the whole point of having co-founders so that you
       | can share the trauma? Why did the CEO have to suffer through so
       | much pain all alone?
        
         | czbond wrote:
         | From much experience with startups, founding and co-founding is
         | a mental mind-f*ck at all times. Even founders of good
         | companies are under constant stress to keep the thing proposed
         | up. The stress and drama of running a company completely f's
         | your world up long into "success"
        
       | Aeolun wrote:
       | I always wonder why people use Twitter for these braindumps? Do
       | these threads just lend themselves well to starting and typing
       | until it's all off your chest?
        
         | [deleted]
        
         | kypro wrote:
         | I quite like it. It promotes a concise writing style which
         | wouldn't be as acceptable if it were on a blog without
         | character limits.
         | 
         | Whenever I write something like this I've found I end up
         | constructing each tweet a bit like a lengthy bullet point. I
         | cut everything unnecessary and try to make my point as clearly
         | as possible in as few words & tweets as possible.
         | 
         | When I write a blog post I naturally end up optimising for
         | writing quality, and what could have been 5 tweets ends up as
         | 1,500 words.
        
       | d3ntb3ev1l wrote:
       | So many fine people on both sides of the Silicon Valley soap
       | opera
        
       | easton wrote:
       | Thread Reader really helps for this, given the length (and some
       | weird issues at least for me with twitter web).
       | 
       | https://threadreaderapp.com/thread/1316730252295454720.html
        
       | regularemployee wrote:
       | I'm not a CEO, nor do the livelihoods of people depend on me.
       | 
       | But I feel the pain everyday of having to answer to my managers
       | who are constantly asking for status on my projects. I care about
       | my managers but I don't care about the projects. I hate my work.
       | 
       | There are so many things in life that I am curious about like
       | singing, drawing, gardening, bird watching, etc. I'm not good at
       | any of them (nor do I wish to be) so they won't bring me any
       | income. Every day I put my curiousness aside to code some stuff
       | to make my managers look good.
       | 
       | I can't quit my job to take a break because my wife and kids
       | depend on my salary for money. My neighbors are suffering more
       | because they are not in tech. They are trying so hard to have my
       | life and I try my best to help them get into an industry I don't
       | even like.
       | 
       | Money brings so much suffering and our entire society is built on
       | it. Society is greedy and wants to expand infinitely too!
       | Everything in nature must eventually be owned my someone.
       | 
       | It seems like the only way to escape is to become a CEO, make
       | millions, and buy a bubble of eternal happiness as Ryan has done.
       | 
       | I hope I don't end up behaving like his former board member.
        
         | tossmeout wrote:
         | Why not just downgrade your lifestyle to be in a cheaper
         | situation? Easier said than done obviously, as that initial
         | downgrade feels like a big hit. And ofc you might have
         | extenuating circumstances that prevent it. But otherwise, I've
         | found that you simply acclimate over time. Then you can give
         | yourself breathing room to take time between jobs, or perhaps
         | move to a lower-paying job you actually enjoy.
        
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       (page generated 2020-10-15 23:00 UTC)